Crafted Journey How To: Mastering Sales Enablement in an AI-Driven Market
Sales enablement is increasingly critical as organizations scale globally, expand product portfolios through acquisition, and navigate an influx of AI tools. Despite its proven impact on win rates and sales cycle length, many companies still struggle to implement it effectively. This piece explores how to master sales enablement in an AI-driven market.
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Key takeaways
AI tools and global growth are putting pressure on sales teams to ramp faster and sell more consistently.
Effective sales enablement can measurably improve win rates and shorten sales cycles.
Many organizations still lack a cohesive sales enablement strategy despite clear business benefits.
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Sales enablement is having a moment—and for good reason. As organizations grow more global, product portfolios expand through acquisition, and AI tools flood the market, sales teams are under pressure to ramp faster, stay consistent, and sell smarter. Effective sales enablement can improve win rates and shorten sales cycles, yet many companies still struggle to align content, messaging, and tools across regions. The stakes are high: without a strong enablement foundation, even the best products can stall in the market.
So what does modern sales enablement actually look like today—and how do leaders build programs that scale without losing clarity or consistency?
Welcome to Crafted Journey. In the latest episode, host Suzy DeLine sits down with Rhett Livengood, Sales Enablement leader at Keyfactor, to unpack what it really takes to master sales enablement in 2026 and beyond. Drawing on decades of experience spanning engineering, manufacturing, software, cybersecurity, and internal startups, Rhett shares practical insights on how enablement has evolved, where AI fits (and where it doesn’t), and why the fundamentals still matter.
What you’ll learn…
- Content, messaging, and assets are the foundation of sales enablement. Rhett explains that despite new tools and trends, these three pillars remain essential for ensuring sales teams deliver consistent value propositions at every stage of the buyer’s journey.
- Sales enablement now lives under intense time pressure. With global teams, higher employee turnover, and AI entering the workflow, onboarding and ramp time have become critical competitive advantages for modern sales organizations.
- AI only works as well as the data and discipline behind it. Rhett cautions that without clean data, clear value propositions, and well-structured playbooks, automation becomes noise rather than a true productivity multiplier.
Rhett Livengood is a sales enablement and partner marketing leader with more than a decade of experience driving revenue growth at the intersection of AI, cybersecurity, and enterprise technology. He spent over 12 years at Intel, where he built global sales and security Centers of Excellence, accelerated partner readiness, reduced sales prep time, and enabled thousands of customers and partners through scalable training and certification programs. Currently at Keyfactor, Rhett leads global sales enablement initiatives that integrate acquired cybersecurity portfolios, accelerate pipeline development, and equip sales and solution engineers with the tools needed to drive digital trust.
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